Direct Substitution of Secondary and Tertiary Alcohols To Generate Sulfones under Catalyst- and Additive-Free Conditions

An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantag...

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Published inOrganic letters Vol. 20; no. 17; pp. 5353 - 5356
Main Authors Liu, Yanan, Xie, Peizhong, Sun, Zuolian, Wo, Xiangyang, Gao, Cuiqing, Fu, Weishan, Loh, Teck-Peng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.09.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROOM-TEMPERATURE
DNA CLEAVAGE
ALLYLIC ALCOHOLS
C BOND
STEREOCENTERS
ALLYLATION
ALPHA-ALKYLATION
REACTIVITY
CROWN-ETHERS
ALKYNES
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Summary:An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02188